ArticleJournal of the American Chemical Society2020
Total Synthesis of (-)-Mitrephorone A Enabled by Stereoselective Nitrile Oxide Cycloaddition and Tetrasubstituted Olefin Synthesis.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Concise synthesis of bufogargarizin B by a conformation-controlled skeletal reorganization approach.Nature communications · 2026Article
- Oxetanes: formation, reactivity and total syntheses of natural products.Beilstein journal of organic chemistry · 2025Review
- Modular Synthesis of New Metalloid-Substituted Olefins from Diboryl(Silyl)Ethenes via Suzuki-Miyaura Reactions.International journal of molecular sciences · 2024Article
- Remote-carbonyl-directed sequential Heck/isomerization/C(spNature communications · 2024Article
- Total syntheses of strained polycyclic terpenes.Chemical communications (Cambridge, England) · 2022Review
- Total Synthesis and Late-Stage C-H Oxidations ofAngewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Article
- Total Synthesis and Late-Stage C-H Oxidations of ent-Trachylobane Natural Products.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
3 authors.
Funding
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Abstract
A highly enantioselective and diastereoselective total synthesis of the diterpenoid (-)-mitrephorone A is presented. Key to the synthesis are stereocontrolled 1,4-semihydrogenation of a 1,3-diene to a tetrasubstituted double bond, enzyme-catalyzed malonate desymmetrization, and highly diastereoselective nitrile oxide cycloaddition. The streamlined strategy is a considerable improvement to those reported earlier in terms of diastereo- and enantioselectivity. For the first time, the combination of modern Pd-cross-coupling with Cr-catalyzed reduction allows for rapid access to tetrasubstituted olefins with full stereocontrol.
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Registered trials
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